Vinyl cyclopropyl compounds as precursors to fatty acid oxidation products

Abstract

A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.

What is claimed as new and is intended to be secured by Letters Patent is: 
     
       1. A method of synthesizing a nucleophile substituted unsaturated hydrocarbon based compound comprising: reacting a compound of the formula: ##STR9## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, carboxyalkyl, carboxyalkenyl, and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic Ag +  salt/H 2  O 2  reagent. 
     
     
       2. A method for synthesizing a nucleophile substituted fatty acid derivative, comprising: reacting a vinyl cyclopropyl group containing fatty acid or ester of the formula: ##STR10## wherein R" is hydrogen, alkyl, aralkyl, or alkenyl or aralkenyl containing at least one olefinic site; L is alkylene of 3 to 9 carbon atoms, optionally containing at least one olefinic site; R''' is hydrogen, alkyl, aryl or aralkyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic Ag +  salt/H 2  O 2  reagent. 
     
     
       3. The method of claim 1, wherein said leaving group X is bromine. 
     
     
       4. The method of claim 1, wherein said reaction is conducted at a temperature of 0° to 40° C. 
     
     
       5. The method of claim 1, wherein said reaction is conducted in a solvent of a dialkylether, a dialkylformamide, acetonitrile, trifluoroethanol, or dimethylsulfoxide. 
     
     
       6. The method of claim 2, wherein in said vinyl cyclopropyl compound reactant, said substituent R''' is methyl, R" is CH 3  (CH 2 ) 4  CH═CH--, X is bromine and L is --(CH 2 ) 6  --. 
     
     
       7. The method of claim 2, wherein said group R is n-butyl, said radical -L- is --CH 2  CH═CHCH 2  CH═CH(CH 2 ) 3  -- and R' is methyl. 
     
     
       8. A method for synthesizing a nucleophile substituted fatty acid derivative, comprising: reacting a vinylcyclopropyl group containing fatty acid or ester of the formula: ##STR11## wherein R'', R''', L and X are as defined above, with a nucleophilic Ag +  salt/H 2  O 2  reagent. 
     
     
       9. A method of synthesizing a nucleophile substituted unsaturated hydrocarbon based compound, comprising: reacting a compound of the formula: ##STR12## wherein R and R' independently are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl or alkoxy and X is a leaving group selected from the group consisting of chlorine, bromine and iodine with a nucleophilic Ag +  salt/H 2  O 2  reagent.